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12 protocols using 3 pentanone

1

Comprehensive Ketone Characterization Protocol

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The following liquid substances were purchased from Sigma-Aldrich: 2-pentanone (98%), 3-pentanone (99%), 2-hexanone (98%), 3-hexanone (98%), 3-heptanone (analytical standard), 4-heptanone (98%), 2-nonanone (99%), 3-nonanone (99%), 2-decanone (98%), cyclohexanone (99.8%), 3-methyl-2-pentanone (99%), 2-methyl-3-pentanone (97%), 2-methyl-3-hexanone (98%), and 2-methyl-3-heptanone (99%). 2-butanone (99.5%), 2-heptanone (98.5%), and 3-methyl-2-butanone (98.5%) were purchased from Honeywell. 3-octanone (99%) and 3-decanone (97%) were purchased from Acros Organics and SAFC, respectively. These were used with no further purification.
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2

Seaweed Iodine Content Quantification

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KI (potassium iodide; puriss. p.a., reag. ISO, reag. Ph. Eur., ≥99.5%), 3-pentanone (ReagentPlus, ≥99.0%), and K2Cr2O7 (ReagentPlus, ≥99.5%) were purchased from Sigma-Aldrich (Sigma-Aldrich, St. Louis, MO, USA). NaOH (ACS, Reag. Ph. Eur) was obtained from Merck (Darmstadt, Germany). H2SO4 (Extra Pure Reagent) was from Union Chemical Works Ltd. (Hsinchu, Taiwan). n-Hexane (≥99%, HPLC grade) was from Tedia (Fairfield, OH, USA). Seaweed samples were purchased from local convenient stores and supermarkets. All seaweed samples were dried seaweeds. The place of origin for all seaweed samples is listed in Table 1.
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3

Authentic Standards for Metabolite Identification

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Authentic standards were co-analyzed and used for confident metabolite identifications [31 (link)]. Authentic standards used were 1-butanol, 1-pentanol, 1-hexanol, 2-pentylfuran, (Z)-3-hexenyl acetate, (E,E)-2,4-heptadienal, (E)-2-octen-1-ol, β-linalool, nonanoic acid (TCI America, Portland, OR, USA); decanal, decanoic acid, β-ionone, 3-pentanone, butyl acetate, benzaldehyde (Sigma-Aldrich Inc., St. Louis, MO, USA); 2,3-butanedione, 1-penten-3-ol, hexanal, myrcene, p-cymene, D-limonene, 1-octanol (Fluka Chemical Co., Milwaukee, WI, USA); isoprene, 1-penten-3-one, pentanal, 2-ethylfuran, 3-methyl-1-butanol, (Z)-2-penten-1-ol, (E)-2-hexenal, 2-ethylthiophene, heptanal, (E,E)-2,4-hexadienal, (E)-2-heptenal, hexanoic acid, 1-octen-3-ol, octanal, benzeneacetaldehyde, (E)-2-octenal, nonanal, 4-oxoisophorone, (E)-2-nonenal, octanoic acid, 2-nonen-1-ol, (E,E)-2,4-nonadienal, (E)-2-decenal, N,N-dibutylformamide (Aldrich Chemical Co., Milwaukee, WI, USA); p-menth-1-en-4-ol (Wako Chemical Co., Richmond, VA, USA); and 1-octen-3-one (Alfa Aesar, Ward Hill, MA, USA). 3-Pentanol (Fluka Chemical Co.) was used as an internal standard. The internal standard was chosen due to its stability, reproducibility, and absence in alfalfa plants.
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4

Detailed Volatile Organic Compound Analysis

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All VOC standards were purchased from Sigma-Aldrich (St. Louis, MO, United States): 1-penten-3-ol, 1-penten-3-one, 3-pentanone, α-caryophyllene, α-farnesene, α-pinene, β-caryophyllene, β-farnesene, β-ionone, benzaldehyde, cis-3-hexen-1-ol, cis-3-hexenyl acetate, eugenol, hexyl acetate, jasmone, limonene, linalool, methyl jasmonate, methyl salicylate, ocimene, trans-2-hexen-1-al. All VOC standards were diluted in 100% methanol.
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5

Synthesis and Characterization of Fluorescent Dextran Derivatives

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2-azidoethyl (2,5-dioxopyrrolidin-1-yl) carbonate and (1R,8S,9S)-bicyclo[6.1.0]non-4-yn-9ylmethyl succinimidyl carbonate were obtained from GalChimia (A Coruña, Spain). 96 Well Half-Area Microplate were acquired from Corning (NY, USA). 3 mL glass vials with 10 mm inner diameter, circular cover glasses of 15mm diameter, 1,5 mL Pierce microcentrifuge tubes and plastic Petri dish Nunc 35 mm diameter were purchased from Thermo Scientific (Toronto, ON, Canada). Tailored Franz cells were acquired from Afora (Barcelona, Spain). Deuterated dimethyl sulfoxide (DMSO-d6), dimethyl sulfoxide (DMSO), acetone, diethyl ether, ethanol (EtOH), nbutanol (BuOH), dichloromethane, ethyl acetate, xylene, cyclohexanone, 1-pentanol, 3-pentanone, ethyl acetoacetate, chloroform and 4 kDa, 20 kDa, 40 kDa, 70 kDa, and 150 kDa FITC-dextran were obtained from Sigma-Aldrich (San Luis, MO, USA).
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6

Profiling Plant Volatile Emissions

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For maize, fully expanded third leaves of wild type (WT) and lox10-3 mutant in the B73 background were enclosed in 800 mL jars (one leaf per jar) alongside a cotton ball containing 2.5 μL of 100 mM of select PLVs dissolved in dichloromethane. For Arabidopsis, intact WT or Atlox2-1 mutants were grown in small pots (∼350 mL) (5 plants/pot), were enclosed in these jars with the respective treatments. Col-0 was exposed to 5 μL of treatments, Atlox2-1 mutants were exposed to 2.5 μL. Four replicates for each plant/genotype/treatment were used. PLV treatments included purified chemical standards of (2Z)-pentenol, (2E)-pentenol, (2E)-pentenal, pentanol, pentanal, 1-penten-3-ol, 1-penten-3-one, 3-pentanol, and 3-pentanone (Sigma-Aldrich, St. Louis, MO, United States). Plants were incubated alongside the PLV treatments for 20 min, and then volatiles were collected onto HaySepQ filters containing 80–100 mesh (Supelco, Bellefonte, PA, United States) via dynamic airflow (1 L min–1) for an additional 20 min. Volatiles were eluted off the HaySepQ filter traps with 250 μL of dichloromethane containing 100 μM of the internal standard, (4Z)-hexenol (Sigma-Aldrich, St. Louis, MO, United States). Volatiles were analyzed and quantified via gas chromatography mass spectrometry (GC-MS).
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7

Volatile Organic Compounds Analysis

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The chemical standards dimethyl sulfide, carbon disulfide, 2‐methyl‐1‐propanal, 2,3‐butanedione, 2‐butanone, chloroform, 2‐methyl‐1‐propanol, 3‐methylbutanal, 3‐methyl‐2‐butanone, 2‐methylbutanal, 2‐pentanone, 1‐penten‐3‐ol, pentanal, 3‐pentanone, acetoin, 3‐methyl‐1‐butanol, methylcyclohexane, dimethyl disulfide, 2‐methyl‐1‐butanol, 2‐penten‐1‐ol, 3‐hexanone, hexanal, ethyl butyrate, 1,2‐dimethylcyclohexane, 1‐hexanol, 2‐heptanone, dimethyl trisulfide, octanal, 2‐ethyl‐1‐hexanol, 2‐nonanone, nonanal, decanal, 2‐undecanone, and 4‐heptanone were purchased from Sigma‐Aldrich. The chemical standards 2,4‐octadiene and 1,1,3‐trimethylcyclohexane were purchased from BOC Sciences. Pentane, n‐heptane, toluene, sodium sulfate (Na2SO4), and anhydrous powder (ACS grade) were purchased from Fisher Scientific.
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8

Synthesis and Characterization of Polymer Electrolytes

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Vinylimidazole (99%), bromoacetonitrile (97%), poly(acrylic acid) (PAA) (Mw—2000 Da), and poly(N,N-dimethyldiallylammonium chloride) (Mw—400,000–500,000 Da) were purchased from Sigma Aldrich (Gillingham, United Kingdom). Lithium bis(trifluromethane sulfonyl)imide (LiTFSI, 99.95%) was purchased from Io-li-tec (Heilbronn, Germany). All chemicals were used without any further purification. Solvents were of analytical grade. Pentanoic acid (>99%), hexanoic acid (>99%), 3-pentanone (>99%), 2-hexanone (>98%), 2-heptanone (>98%), 2-methylbutanal (98%), 1-heptanal (95%), 1-hexanol (99.9%), 2–heptanol (98%), 1–octanol (99.7%), benzyl alcohol (99.8%), 1-ethylnaphtalene (>97%), carvacrol (>98%), (+)-α-pinene (>99%), α-terpineol (>99%), eucalyptol (99%), (R)-(+)-pulegone (97%), and β-citronellol (95%) were purchased from Sigma-Aldrich (Gillingham, United Kingdom). BTEX: Benzene (B) (99%) was provided by Riedel-de Haen, (Charlotte, NC, USA). Toluene (T) (99%), ethylbenzene (E) (99%), and p-xylene (X) (99%) were obtained from Merck (Darmstadt, Germany).
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9

Flavor Compound Identification and Quantification

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Acetone, trimethylamine, 1-propanol, dimethyl sulfide, 2-methyl-1-propanol, 1-penten-3-ol, (z)-2-penten-1-ol, 3-pentanone, 3-methyl-butanal, 2-methyl-1-butanol, 1-pentanol, 3-pentanol, phenol, methyl-pyrazine, 2-ethyl-furan, 2-furanmethanol, propyl acetate, 1-hexanol, benzyl alcohol, 2,3-dimethyl-pyrazine, 2,5-dimethyl-pyrazine, 1heptanol, 2-ethyl-5-methyl-pyrazine, phenylethyl alcohol were purchased from Sigma-Aldrich (Shanghai, China). Mequinol, 2, 2, acetic acid, propanoic acid, acetoin, styrene, China) . The purity of these flavor standards was more than 99%. The n-alkanes (C6 to C30) were acquired from Sigma-Aldrich (Shanghai, China). The isotope internal standards (n-nonan-d20, n-dodecane-d26, n-nonadecane-d40, n-tridecane-d28, n-hexadecane-d34) were purchased from Cambridge Isotope Laboratories, Inc.
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10

Synthesis of Cobalt-based Metal-Organic Frameworks

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Cobalt nitrate hexahydrate [Co(NO3)2·6H2O], 2-methylimidazole (99%), N, N-dimethylformamide (DMF, 99.5%), ethanol (EtOH, 98%), acetone (CH3COCH3, 99.5%), cyclohexane (C6H15, 99%), 4-methyl-1-hexene (C7H14, 99.5%), 3-pentanone (C5H10O, 99%), and toluene (C7H8, 99.8%), were purchased from Merck (South Africa). Lighthouse candles were purchased at a local supermarket in Johannesburg, South Africa.
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